1-Iodonaphthalene → HCID 11746284, compound

HRID 984516Notes

Reaction equation

HRID 984516 reaction equation
O([Si](C)(C)C)[K].I[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH:17](/[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 70041-IodonaphthaleneHCID 178504318HCID 178504318, compound

Product 1

HCID 11746284HCID 11746284, compound

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

Following General Procedure II, a mixture of KOSiMe3 (570 mg, 4.0 mmol, 2.0 equiv), (Z)-21 (379 mg, 2.2 mmol, 1.1 equiv), 1-iodonaphthalene (292 μL, 2.0 mmol) and Pd(dba)2 258 mg, 0.1 mmol, 0.05 equiv) was stirred at room temperature for 9 h, and then was filtered through SiO2. Purification by column chromatography (RP C18, MeOH/H2O, 9/1) and Kugelrohr distillation afforded 394 mg (88%) of (Z)-154a as colorless oil.

Workup

  1. filtrationwas filtered through SiO2
  2. customPurification
  3. distillationby column chromatography (RP C18, MeOH/H2O, 9/1) and Kugelrohr distillation
  4. customafforded 394 mg (88%) of (Z)-154a as colorless oil

Sources & evidence

ORD record
ord-a65fdc6b03724e51bb2058a89af88c9c
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

Loading…